The Jake Gyllenhaal Career Matrix: From ‘Donnie Darko’ to ‘Southpaw,’ and All the Essential Roles In Between

Open Road

On Friday, Jake Gyllenhaal’s boxing movie, Southpaw, will release into thousands of theaters nationwide. This is news that is excellent in general, but also excellent for me personally. Jake Gyllenhaal is an interesting actor with an interesting face who makes interesting creative choices, and so him being in a movie directed by the same person who directed Training Day is something that is easy for me to get excited about. I suppose there’s a chance that it could be bad, but that seems unlikely. So we’re all just a couple of days away from watching something that has a high probability of being one of my favorite movies of all time. Aren’t you happy for me?

Another thing I should mention is that I am sort of in love with Jake Gyllenhaal. I didn’t realize that this was the case until last March, which I wrote about here, but I am aware of it now, and so I’m always seeking out all of the Gyllenhaal-related content I can find. And now I’m making some more: This is The Jake Gyllenhaal Career Matrix. It’s about celebrating many of the roles Jake Gyllenhaal has played over the course of his career. This is not a difficult thing to understand, so I will do my best in the coming moments not to make it so. In fact, I will do the least difficult thing I can think of, which is to answer fake questions that I’m asking myself.

What am I about to look at?

The Jake Gyllenhaal Career Matrix.

What does that mean?

Well, it means you’re going to look at an infographic that examines the roles Jake Gyllenhaal has played in movies over the past 15 or so years and identifies how they relate to one another in the Jake Gyllenhaal universe, which, FYI, is a universe I would very much like to live inside of.

What, precisely, does the matrix do?

It charts the locations of 16 separate Gyllenhaal movie roles, placing them in quadrants based on their individual qualities, specifically as each concerns coolness, uncoolness, wimpiness, and toughness. All the way up at the top are his least cool characters and all the way at the bottom are his most cool. All the way to the left are his wimpiest roles, all the way to the right are his toughest, and when I say “toughest” I mean “tough guys in the movie,” not “tough for Gyllenhaal to portray,” which is an important distinction to make. It’s important that you remember that we’re only ever looking at the character and the events and circumstances that surround said character.

How were the roles chosen?

A longer list of about 30 or so roles was made first. (There was no preference given to the time period of Gyllenhaal’s career that a role occurred in or even the amount of screen time afforded a role, though obviously movies he starred in were at an advantage.) Over a handful of emails and several especially aggressive Google Hangouts with some trusted advisers, the list of 30 was culled down to 20 roles. Then those 20 were all weighted and given a cumulative score based on important things like the depth of the role’s cultural impact, regularity of its occurrence in pop culture, and whether or not Gyllenhaal took his shirt off for it. Those 20 were then cut down to the final 16. And those 16 were all placed in the matrix.

That seems like a lot?

Yeah, I’m kind of churching it up some. Mostly, I just picked the ones I wanted to and plugged them in where they belonged.

I don’t see my favorite role on here. To whom should I complain?

Yo mama. There were way more Gyllenhaal roles than there were available spaces on the matrix. And we only needed the 16 to fill in the box. Let’s not make a great big stink about it, OK?

This started out sounding legit, but it’s devolving pretty quickly. Perhaps we should just get to the matrix?


Before we get to the actual matrix, a peek at a few roles that ended up getting squeezed out of it:

City Slickers

Role: Danny Robbins

Jake has a teeny part in it. It’s inconsequential, really. But, still. The video above, that’s him talking. Listen to it. His part is only a few seconds long, but it is all the way worth it, particularly if you’re smitten with Gyllenhaal right now. His voice is extra tiny. It’s startling to hear.

Sidebar: In the clip, Jake is introducing his dad, Billy Crystal, to his class for career day. Embarrassed by what he considers to be his dad’s boring job (selling radio commercial space to companies), Jake tells the kids that he’s a submarine commander instead. That’s such a devastating blow to have to absorb when you’re a dad. I am not looking forward to that happening to me. There’s no way I make it through that situation without telling whichever one of my sons does it to me to eff off.

October Sky

Role: Homer Hickam  

Deserves an ancillary mention here because Chris Cooper played Jake’s disapproving father in it. Later that same year, he played the disapproving father in American Beauty, too. Apparently, 1999 was a tough year for Chris Cooper’s movie kids.


Role: Harold Dobbs

It was a serviceable movie if you squinted hard enough, but it was completely washed away because it came out in between Brokeback Mountain and Jarhead, two iconic Gyllenhaal performances. Proof is the Sam Bowie of Jake Gyllenhaal’s career, I suppose.

The Good Girl

Role: Holden Worther

I have so much respect for Jennifer Aniston’s hustle in The Good Girl because she goes from having to kiss John C. Reilly,who basically looks like someone taught a bear to wear shirts, to getting to kiss Jake Gyllenhaal, who is 100 percent worth the trouble of teaching your iPhone to spell his last name. Very real question: How big of a bear would you try to fight to death for the chance to marry Jake Gyllenhaal? I feel comfortable saying I’d go up to 50 pounds. Any bear above 50 pounds is likely going to kill me before I kill it. And neat as it’d be to die by the hands (paws) of a bear, I’d just as soon avoid it, if possible.


JG Matrix Final Version


Now that you’ve seen the matrix, some important notes:

The most compelling haircut of any Jake Gyllenhaal character is Detective Loki from Prisoners and it’s not even close.


Fact. Imagine you had that hair, so thick and lush that it almost seems its own entity, something that becomes less like hair atop his head and more like a down comforter for his skull. I’ve never been as good at anything as Detective Loki is at having hair and I’ll never get that good at anything, either.

The Jake Gyllenhaal Movie Role Toughness Index (the x-axis on the matrix) is a very real thing.

He covers the entire spectrum. On the one end, you’ve got his role in Bubble Boy (Jimmy Livingston), where he was literally so sickly that he had to live in a bubble. And way, Way, WAY on the other end you’ve got Southpaw (Billy Hope), where he is a jilted professional boxer living under dire circumstances. He’s made out of warm goop in Bubble Boy. He’s made out of laser-chiseled titanium in Southpaw. I’m not sure we’ve seen anybody so obviously hit the corners like that. Maybe Sean Penn (I Am Sam and Mystic River)? Maybe Arnold Schwarzenegger (Junior and Commando)? Maybe Brad Pitt (the old man-baby in The Curious Case of Benjamin Button and Fight Club). Those feel like reaches, though. The most comparable jump is (probably) the one Morgan Freeman pulled off, going from playing a driver for a white woman in rural Atlanta in Driving Miss Daisy to playing God in Bruce Almighty, but that wasn’t a toughness thing, at least not the kind of toughness we’re measuring here.

(The one gripe I heard about the Southpaw placement was that it should’ve been swapped with his role in Jarhead (Anthony Swofford), where he played a Marine sniper. That’s a fair point to bring up, albeit one that’s ultimately incorrect, even if you’re only playing percentages. Because what did we really see Gyllenhaal do in Jarhead that you could make a toughness-based argument for besides just being a Marine? He mostly complained a lot and danced around with a Santa hat on his genitals.

What’s up with Prince of Persia: The Sands of Time?

Uncool? Desperately. Wimpy? Not a chance. He was a street-urchin-turned-prince WHO COULD TRAVEL THROUGH TIME. Time travel made George McFly brave enough to fight Biff and George McFly was built like Taylor Swift. You give a yoked-up Dastan a sword and the ability to move through time and you’ve got yourself a goddamn problem, my friend.

Please explain Enemy to me.

I have no idea. Is this movie incredible or was it awful?1 Is it suspense or was it horror or some percentage of both? Is Jake Gyllenhaal a genius for doing this or a clown for doing it? Who’s real in it? Who’s fake? Are they the same person? Different people? Why does his mom not know anything? What’s going on with the blueberries? What’s going on with the sex club? What’s going on with the pregnant woman? Why did he not even flinch at the end? WHY DID HE NOT EVEN FLINCH AT THE END? My heart shot out of my eye sockets at the end and all he did was look – is “resigned” the right word? — all he did was look resigned. Is that what he looked like? Who cares where it goes on the matrix because how can I ever even live my life again with any sort of semblance of normalcy after watching Enemy??? WHAT DO I DO NOW???

Is Jake’s role in End of Watch (Brian Taylor) incorrectly placed?

No, it’s not. I get that you’d feel that way – when I emailed an initial version of this chart out for opinions that was one of the things that was brought up the most. And as a reflexive response, I understood it. I understand it. End of Watch was incredible. When I was teaching, I was work friends with the guy who was in the classroom next to mine for nearly a decade. The only things he ever bothered to talk to me about were his son — of whom he was endlessly proud because he’d made it through high school and had gotten into an honors program at a very good school — and End of Watch, which, hand to God, he said was the only thing that’d made him cry since his mother passed. It’s a very intense, very great movie. But if you look specifically at Brian, if you look at only the decisions that that character made and the ramifications that followed, then it’s extra easy to see: not that cool of a person.

Also: Is that really where Brokeback Mountain (Jack Twist) belongs on the matrix?

Yes. A hundred times yes. There’s nothing cooler than a man who is in love and there are very few things tougher than a man who has to synthesize the cognitive dissonance that was rumbling around inside Jack Twist’s head.

What’s the best overall role of Jake Gyllenhaal’s career?

It’s his Louis Bloom in Nightcrawler. It’s maybe an overacted role, but one that’s still compelling and exceptional. I’ve always liked how Wesley Morris ended his review of the movie. It seemed to be the best summation of Gyllenhaal and Bloom: “Gyllenhaal can appreciate that he’s not a conventional star, and there may be no acting challenge in stardom for him anyway. He needs psychology to play. Nightcrawler might give him too much. It’s like he’s been cramming for greatness. But there’s a crazy spark to him here nonetheless. The performance captures the delusion of talent. Louis is a carrion maggot who’s mistaken himself for Weegee.”

This is the no. 1 scene from Nightcrawler. It happens near the end of the movie, when Louis negotiates to sell some very prime kill footage to the station manager he’s been selling his clips to (and also sleeping with in a prearranged deal). It’s right here when he finally meshes his psychoses with his business acumen fully:

In 2014, Gyllenhaal was being interviewed by Nightline about the movie. They asked him what sort of preparation he’d done for the role, physically and emotionally. He responded — and he said this seriously — “I wanted [Bloom] to look like a coyote. And in order to do that I had to look hungry and be hungry.” Then he talked about going for long runs at night and imagining he was a coyote. Then he blinked those bowling ball eyes and smiled that weirdly charming smile. I felt like I was watching a coyote.

And that’s why this is the greatest role of his career.


Filed Under: Movies, Southpaw, Enemy, Brokeback Mountain, prisoners, End of Watch, Jake Gyllenhaal

Shea Serrano is a staff writer for Grantland. His latest book, The Rap Year Book: The Most Important Rap Song From Every Year Since 1979, Discussed, Debated and Deconstructed, is a New York Times best seller and is available everywhere.

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